Which JR pass please

Hi there, we will be arriving in Osaka aiport, spending 2 nights in Osaka and then wish to visit Hiroshima for 1 night, Kyoto for 4 nights to include Nara, Walk the Nakasendo between nakatsugawa and Narai, (3) visit Kanazawa (2) and Tokyo possibly heading out to walk mt matake too.(4) We have three weeks. Given we are staying in places for more than one night is the 3 week pass cost effective. Getting so confused! We also have an extra 5 days and thought we may fly to Ishigaki at the end from Tokyo. Would you have any recommendations as to the order we visit the places given rail connections or other places we should consider to fill the remaining 4/5 days please. Im not sure the 3 week pass is worth it but the 7 days passes would mean rushing to get everywhere.Thank you so much for any advice